(2S,3R)-1-Iodo-4-(benzyloxy)-2,3-butanediol | 156038-50-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3R)-1-Iodo-4-(benzyloxy)-2,3-butanediol
• 英文别名: (2R,3R)-1-(Benzyloxy)-4-iodo-2,3-butanediol；(2R,3R)-1-iodo-4-phenylmethoxybutane-2,3-diol
• CAS: 156038-50-5
• 化学式: C₁₁H₁₅IO₃
• 分子量: 322.143
• InChiKey: NGVKRKUNYHASSB-WDEREUQCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  15
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-1-Iodo-4-(benzyloxy)-2,3-butanediol 在 偶氮二异丁腈 、 三正丁基氢锡 作用下， 以 乙二醇二甲醚 为溶剂， 反应 1.0h， 生成 (2R,3S)-1-(Benzyloxy)-2,3-butanediol
  参考文献：
  名称：

  C-1 Reactivity of 2,3-Epoxy Alcohols via Oxirane Opening with Metal Halides: Applications and Synthesis of Naturally Occurring 2,3-Octanediol, Muricatacin, 3-Octanol, and 4-Dodecanolide

  摘要：

  The C-1 reactivity of 2,3-epoxy alcohols and derivatives has been examined thoroughly. In the first approach a rearrangement opening of 2,3-epoxy alcohols with LiI leads to 1-iodo 2,3-diols with erythro or three stereochemistry starting from trans or cis epoxy alcohols. Subsequent coupling with a carbon nucleophile can lead to a series of vicinal diols with predicted relative and absolute stereochemistry: the described methodology has been applied to the asymmetric synthesis of the naturally occurring (S,S)-2,3-octanediol and (R,R)-muricatacin. The second approach, starting from easily available tosyloxy epoxides, leads to the highly regioselective opening of the oxirane ring with Li halides. The 3-iodohydrins obtained can be reduced to the corresponding 1-(tosyloxy)alkan-2-ols and then coupled with common carbon nucleophiles to afford, in high yields, optically active alcohols. This methodology has been applied to the asymmetric synthesis of naturally occurring pheromones like 3(R)-octanol and 4(R)-dodecanolide.

  DOI：

  10.1021/jo00120a025
• 作为产物：
  描述：

  (2R,3R)-1-(Benzyloxy)-4-<(tert-butyldimethylsilyl)oxy>butane-2,3-diol cyclic sulfate 在 硫酸 、 溶剂黄146 、 sodium iodide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.5h， 生成 (2S,3R)-1-Iodo-4-(benzyloxy)-2,3-butanediol
  参考文献：
  名称：

  An Access to erythro-Diols via Sharpless's Asymmetric Dihydroxylation Reaction

  摘要：

  A method has been developed to access erythro-2,3-diols via Sharpless's asymmetric dihydroxylation reaction. Thus, a TBDMS-protected (E)-allylic alcohol is dihydroxylated and the resulting threo-2,3-diol is converted to the cyclic sulfate. Upon desilylation, this compound undergoes a Payne-type rearrangement. Nucleophilic epoxide-opening then provides an erythro-2,3-diol. The conversions from the cyclic sulfate to the diol product are performed in a single reaction vessel. Due to the irreversible nature of the Payne-type rearrangement, this process is easy to perform and completely regioselective independent of the substrate structures. Also, being performed in THF, the process is compatible with a variety of nucleophiles, including thiolates, N--(3), (OAc)-O--, (CN)-C--, halides as well as carbon nucleophiles and hydride.

  DOI：

  10.1021/jo00088a045